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| Titel: |
Synthesis of the Four Configurational Isomers of N-Benzoyl-2, 3, 6-Trtdeoxy-3-C-Methyl-3-Amino-L-Hexose from the (2S, 3R)-Diol Obtained from α-Methylcinnamaldehyde by Fermentation with Baker'S Yeast |
| Auteur: |
Frenza, Giovanni Fuganti, Claudio Grasselli, Piero Pedrocchi-fantoni, Giuseppe |
| Verschenen in: |
Journal of carbohydrate chemistry |
| Paginering: | Jaargang 2 (1983) nr. 3 pagina's 225-248 |
| Jaar: |
1983 |
| Inhoud: |
The erythro and threo chiral C5 methyl ketones (4) and (5), prepared from the (2S, 3R)-methyl diel (1b), were converted into the phenylsulfenimines (6) and (7), which, in turn, on reaction with allyl-magnesiutn bromide, yielded after acid hydrolysis and benzoylation, the diastereoisomeric C8-N-aminodiol derivatives (9) and (11), with threo stereochemistry relative to positions 4 and 5. Ozonolysis of (9) and (11) yielded the l-arabino and l-xylo 3-O-methyl branched aminodeoxysugar derivatives (13) and (15), respectively. Using diallylzinc as the reagent, the diastereoisomeric erythro products (8) and (10) were obtained. The latter materials gave the l-ribo-and l-lyxo-(lL-vancosamine) derivatives (12) and (14) upon oxonolysis. The 1H and 13C NMR spectra of the four isomeric aminodeoxysugar derivatives (12)—(15) were discussed. |
| Uitgever: |
Taylor & Francis |
| Bronbestand: |
Elektronische Wetenschappelijke Tijdschriften |
Details van artikel 212 van 252 gevonden artikelen
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